Trimethyl orthoacetate → HCID 178433957, compound

HRID 1984029Notes

Reaction equation

HRID 1984029 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]([C@H:12]2[CH2:17][CH2:16][C@H:15]([O:18][C:19]3[CH:28]=[CH:27][C:22]([C:23]([NH:25][NH2:26])=[O:24])=[CH:21][CH:20]=3)[CH2:14][CH2:13]2)=[O:11])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[C:29](OC)(OC)(OC)[CH3:30]>>[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]([C@H:12]2[CH2:17][CH2:16][C@H:15]([O:18][C:19]3[CH:20]=[CH:21][C:22]([C:23]4[O:24][C:29]([CH3:30])=[N:26][N:25]=4)=[CH:27][CH:28]=3)[CH2:14][CH2:13]2)=[O:11])[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 15050Trimethyl orthoacetateHCID 178456383HCID 178456383, compound

Product 1

HCID 178433957HCID 178433957, compoundYield 14%

Conditions

Temperature
120 °C

Procedure

A mixture of 100 mg (0.26 mmol) of trans-4-[4-(4-Isopropyl-piperazine-1-carbonyl)-cyclohexyloxy]-benzoic acid hydrazide and 4 ml of trimethyl orthoacetate was stirred for 10 min at 120° C. using microwave reactor. After evaporation, the mixture was diluted with AcOEt, washed with saturated NaHCO3 solution, water and brine, dried over Na2SO4, and evaporated. The residue was purified by column chromatography on silica eluting with dichloromethane and methanol=from 98:2 to 19:1. The combined product fractions were evaporated to dryness to yield 15 mg (14%) of the title compound. MS (m/e): 413.4 (MH+).

Workup

  1. customAfter evaporation
  2. additionthe mixture was diluted with AcOEt
  3. washwashed with saturated NaHCO3 solution, water and brine
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica eluting with dichloromethane and methanol=from 98:2 to 19:1
  7. customThe combined product fractions were evaporated to dryness

Sources & evidence

ORD record
ord-64bf3745132d404a8fd45fe83d5f0d87
Source dataset
uspto-grants-2009_06
Patent number
US07544683B2

Reaction notes

Loading…